Sweater: Tippi Colorblock Sweater (J.CREW, $95)

From Left, Earrings: Moran Drusy Earrings ($88) Bag:  Iiibecca Moore Satchel ($188) Shoes: VC Signature Francoise ($250) Top: J.CREW Tie Neck Top ($110) Skirt: Rebecca Taylor Sanesi Skirt ($125)

From Right, Sunglasses: Ray Ban Top Bar Aviators ($160) Bag: Coach Legacy Penny Purse ($198) Shoes: Report Rudy Flat Boot ($120) Necklace: Diosa KEZEN Necklace ($677) Jeans: J.CREW Distressed Toothpick Jeans ($168)

Polyvore Set Here.

For the Office. This look has a slightly retro vibe that can be a great way to switch up your look from time-to-time.  If you choose to wear it all the time, however, you could end up looking a bit like you’re trapped in a twee time warp.  See: Zooey Deschanel.

The skirt has a small flounce at the bottom to make it more interesting than your basic pencil.  The blouse is a short sleeve tie neck to prevent excess bulk on the arms.  And both pieces coordinate well with the colors in the sweater.

No, you’re not hallucinating.  Those shoes are black.  No, I did not mean to do that.  My parents’ pre-war computer just has some issues with color.  So how about we pretend they’re not there and superimpose these t-strap Franco Sarto pumps instead?  And if you really like the look of the chunky heeled pump, those VC Signature heels also come in berry and teal, which could work if you chose a neutral bag.

I chose this deep green bag because I wanted to bring in another color and thought that this simple satchel was really a cool piece.  But if green isn’t your thing, the bag comes in several colors including tan and orange.

For the hair, I would wear it up in a twisted updo.  For the makeup, I’d choose a berry-colored lip and light blush with a neutral eye palette.  I would also paint my nails a deep ruby red.

For Wine Tasting.  I wanted to create a truly casual outfit, so I chose a distressed jean and a flat boot.  This is not an office-appropriate jean, but every woman should have one pair of truly comfortable, worn-in jeans for the weekend.  If the skinny style does not appeal to you, GAP has a nice pair of lightly distressed bootcut jeans.

I chose this sickeningly expensive necklace because I loved it.  If you’re crafty, you could probably make your own in the same color palette.  If you’re not, Endless has a similar version for under-$75 (though the colors aren’t quite as lovely).  If you want to skip the necklace entirely, this would be a great place to add an ivory or grey or aqua scarf.

The rest of the accessories were chosen to enhance the casual feel of the outfit without sacrificing style.  This boot is super cute for the autumn.  I am smitten with the tassels on this Coach Legacy crossbody, however, this perfect fall bag comes in a tassel-free, saddle-shaped version as well.  And the top bar aviators just scream cool.

For the hair, I would choose whatever style will look best after four hours drinking wine with your friends.  For me, that would be a low side braid.  For the makeup, I’d go easy on the spackle for such a relaxed look.  Opt for a natural-looking blush, a tinted moisturizer and a light touch with some brown eyeliner.  Also, make sure to add primer and choose a long wear, smudge proof mascara.  A bit of intoxication can look like public drunkenness once the makeup starts to melt.